#116. Boston (Friday, July 31, 2015)

What was your best day…of taking an average family trip?

Thanks to the regret that remained from my younger years (#119), my mom could’ve suggested anywhere for this five-day family trip and I would’ve been down.

Boston turned out to be a great pick.

We packed a lot into the trip, visiting most of Boston’s landmarks along with the fancy mansions in Newport, Rhode Island and the U.S. Military Academy at West Point, while staying at an absolutely massive hotel in Burlington that was an experience in itself.

But the highlight of the trip was the second day, where in the span of a morning and afternoon we went on tours of Harvard, MIT, and Fenway Park—the (only) three iconic things I’d associated with that famous city for as long as I can remember.

Even though my brother was the one going into his senior year of high school and applying to universities in the fall, Harvard and MIT were more for me than him. I’d tried the whole “do the SATs and apply to Ivy League schools” thing eight years earlier and failed miserably, and so I was hoping to live vicariously through him getting accepted to one of those schools—even though he never really had a strong interest.

In any case, actually setting foot on the campuses and interacting with them did a lot to break the insecurity-based aura I’d placed around the schools since my rejections. It was the usual “these are all normal students, and ultimately just universities like the one I attended” experience that comes around to everyone sooner or later. But I was legitimately surprised by the very cool yet down-to-earth MIT vibe, thanks to the most self-deprecating tour guide I’d ever had. (Though this was detracted in part by the members of some Chinese cultural group aggressively accosting my brother and I while we were waiting for our tour.)

As for Fenway Park, beyond the awesomeness of walking through every odd corner the hundred-year-old ballpark (and hearing about pieces of its history I didn’t even know), the coolest part was during the tour, when we saw a long line of Red Sox players standing along the left field foul line—in the middle of doing the Ice Bucket Challenge. All the while, Chris Archer from the visiting Rays was just chilling in the outfield methodically doing his drills, oblivious to all of it.

As if that wasn’t enough baseball, that day was also the MLB trade deadline. Specifically, the 2015 MLB trade deadline: when, in the span of forty-eight hours, the Blue Jays (my favorite team) infamously acquired superstar David Price and several other key pieces that immediately led to an unforgettable two-month playoff push. Two months whose pure magic felt like a continuation of this already great visit to Boston.

Much more on that later.